While thinking of Key West, many conjure up an image of hammock-lined palm trees, pristine water, and refreshing cocktails. It is an accurate description, but unbeknown to some is the rich history the island shares with curious travelers and locals. Its unique location – just 90 miles to Cuba – positioned Key West as a strategic base for military and government operations. The area is home to three Civil War-era forts and was also the birthplace for Pan American Airlines. Here is just one example of a day spent exploring Key Wests legendary landmarks and museums.
Grab an early breakfast and get a jump start on your historical tour by visiting the Key West Cemetery. (There is very little shade so visiting in the morning is best before the sun is out in full force.) See the cheeky epitaphs like "I Told You I Was Sick" and "At Least I Know Where He's Sleeping Tonight" covering the gravestones. The tombs are stacked above ground since the rocky soil made digging down impossible. The main entrance offers a map that details some of the more interesting plots, and you may want to bring crayons and paper for “grave stone rubbings,” unusual – and free – souvenirs.
Robert the Doll at East Martello Museum — Photo courtesy of flickr.com/cayoboNext, wander the stone halls of East Martello, a Civil War-era fort that was never completed, and is now home to numerous exhibits. Learn about American Indians and early settlers, Spanish ship wreckers, Key West’s sponge business, and scuba diving. The newest exhibit, the Ghosts of East Martello features spooky legends like Robert the Doll, and the odd and disturbing tale of the Count and Elena. The museum also showcases wood cuts and painting from artist Mario Sanchez that demonstrates what the island looked like in the 1920s as well as funky, recycled art sculptures from Stanley Papio.
Take a lunch break at Kelly's Caribbean Bar, known as the birthplace for Pan American Airlines (the first tickets were sold there). Kelly's is now a brewery and grill where patrons can order their drinks from the wing of a plane. Once owned by Kelly McGillis (of Top Gun), the actress herself invented many of the sauces used. Sample some of the excellent home-brewed beers like Havana Red, Key West Golden, Southern Clipper Wheat under the canopy of the shaded garden; it is the only brewery left in the Florida Keys. If you're stopping in for a bite, try the pineapple coconut bread and coconut encrusted Mahi Mahi.
Inside the Key West Lighthouse Museum — Photo courtesy of Amber NolanFinish off the day with a stop at Key West's iconic lighthouse, built in 1847 and originally powered by 15 oil lamps that helped guide sailors to the island. Although it no longer serves as a functioning lighthouse, visitors can climb the 88 winding steps to the top for 360-degree views of the city and the ocean. Admission includes entrance to the museum (the former keeper's quarters), where audio and visual recordings are available as well as glass display cases of the previous owner's possessions.